title: A tetraene aldehyde as the major sex pheromone component of the promethea moth (Callosamia promethea (Drury)).
abstract: The promethea moth Callosamia promethea is one of three species of silkmoths from the genus Callosamia that occur in North America. Cross attraction of males to heterospecific calling females has been observed in the field, and hybrid progeny have been produced by pairing heterospecifics in captivity. These observations suggest that all three species share or have considerable overlap in the sex attractant pheromones produced by females, so that other prezygotic isolating mechanisms, such as diel differences in reproductive activity, limit hybridization in the field. Coupled gas chromatography-electroantennogram detection and gas chromatography- mass-spectrometry analyses of extracts of volatiles collected from female promethea moths supported the identification of (4E,6E,11Z,13Z)-hexadeca-4,6,11,13-tetraenal [(4E,6E,11Z,13Z)-16:Ald] as the compound in extracts that elicited the largest responses from antennae of males. The identification was confirmed by non-selective synthesis of several isomers as analytical standards, and stereoselective synthesis of (4E,6E,11Z,13Z)-16:Ald for testing in field trials. Male moths were strongly attracted to synthetic (4E,6E,11Z,13Z)-16:Ald, suggesting that this compound is the major and possibly the only component of the sex pheromone of these large saturniid moths. Based on the cross-attraction of heterospecifics, it is likely that this is also a major pheromone component of the other two North American Callosamia species as well.
authors.affiliation: Department of Biological Chemistry and Molecular Modeling, IQAC (CSIC), Jordi Girona 18, Barcelona, 08034, Spain.
authors.forename: Rafael
authors.initials: R
authors.lastname: Gago
authors.forename: Jeremy D
authors.initials: JD
authors.lastname: Allison
authors.forename: J Steven
authors.initials: JS
authors.lastname: McElfresh
authors.forename: Kenneth F
authors.initials: KF
authors.lastname: Haynes
authors.forename: Jessica
authors.initials: J
authors.lastname: McKenney
authors.forename: Angel
authors.initials: A
authors.lastname: Guerrero
authors.forename: Jocelyn G
authors.initials: JG
authors.lastname: Millar
mesh_terms: D000447:Aldehydes / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D005260:Female; D008297:Male; D009036:Moths / Q000737:chemistry* / Q000187:drug effects*; D009279:Naphthacenes / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D012724:Sex Attractants / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D052617:Solid Phase Microextraction
chemical_list: D000447:Aldehydes; D009279:Naphthacenes; D012724:Sex Attractants; C000589455:hexadeca-4,6,11,13-tetraenal; C487736:naphthacene